N-[(3S)-2-Oxotetrahydro-3-furanyl]nonanamide

Modify Date: 2024-01-08 18:38:50

N-[(3S)-2-Oxotetrahydro-3-furanyl]nonanamide Structure
N-[(3S)-2-Oxotetrahydro-3-furanyl]nonanamide structure
Common Name N-[(3S)-2-Oxotetrahydro-3-furanyl]nonanamide
CAS Number 177158-21-3 Molecular Weight 241.327
Density 1.0±0.1 g/cm3 Boiling Point 456.8±34.0 °C at 760 mmHg
Molecular Formula C13H23NO3 Melting Point N/A
MSDS N/A Flash Point 230.0±25.7 °C

 Use of N-[(3S)-2-Oxotetrahydro-3-furanyl]nonanamide


Quorum sensing is a regulatory system used by bacteria to control gene expression in response to increased cell density. This regulatory process manifests itself in a variety of phenotypes, including biofilm formation and virulence factor production. Coordinated gene expression is achieved through the production, release and detection of small diffusible signaling molecules called autoinducers. N-acylated homoserine lactones (AHLs) comprise a class of such autoinducers, each of which generally consists of a fatty acid coupled to a homoserine lactone (HSL). Modulation of bacterial quorum-sensing signaling systems to suppress pathogenesis represents a new approach to antimicrobial therapy for infectious diseases. AHLs differ in acyl length (C4-C18), C3 substitution (hydrogen, hydroxyl, or oxo group), and the presence or absence of one or more carbon-carbon double bonds in the fatty acid chain. These differences confer signaling specificity through the affinity of the LuxR family of transcriptional regulators. C9-HSL is a rare odd-numbered acyl carbon chain produced by wild-type Erwinia carotovora strain SCC 3193 grown in nutrient-rich Luria-Bertani broth (LB) medium.

 Names

Name N-nonanoyl-L-Homoserine lactone
Synonym More Synonyms

  Biological Activity

Description Quorum sensing is a regulatory system used by bacteria to control gene expression in response to increased cell density. This regulatory process manifests itself in a variety of phenotypes, including biofilm formation and virulence factor production. Coordinated gene expression is achieved through the production, release and detection of small diffusible signaling molecules called autoinducers. N-acylated homoserine lactones (AHLs) comprise a class of such autoinducers, each of which generally consists of a fatty acid coupled to a homoserine lactone (HSL). Modulation of bacterial quorum-sensing signaling systems to suppress pathogenesis represents a new approach to antimicrobial therapy for infectious diseases. AHLs differ in acyl length (C4-C18), C3 substitution (hydrogen, hydroxyl, or oxo group), and the presence or absence of one or more carbon-carbon double bonds in the fatty acid chain. These differences confer signaling specificity through the affinity of the LuxR family of transcriptional regulators. C9-HSL is a rare odd-numbered acyl carbon chain produced by wild-type Erwinia carotovora strain SCC 3193 grown in nutrient-rich Luria-Bertani broth (LB) medium.
Related Catalog

 Chemical & Physical Properties

Density 1.0±0.1 g/cm3
Boiling Point 456.8±34.0 °C at 760 mmHg
Molecular Formula C13H23NO3
Molecular Weight 241.327
Flash Point 230.0±25.7 °C
Exact Mass 241.167801
PSA 55.40000
LogP 1.55
Vapour Pressure 0.0±1.1 mmHg at 25°C
Index of Refraction 1.476

 Synonyms

Nonanamide, N-[(3S)-tetrahydro-2-oxo-3-furanyl]-
N-[(3S)-2-Oxotetrahydro-3-furanyl]nonanamide